Triethylamine → N-Methoxy-N-methyl-1,3-thiazole-5-carboxamide

HRID 928735

반응식

HRID 928735 반응식
C(N(CC)CC)C.[S:8]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9]1.Cl.[CH3:17][NH:18][O:19][CH3:20].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:20][O:19][N:18]([CH3:17])[C:13]([C:12]1[S:8][CH:9]=[N:10][CH:11]=1)=[O:15]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 84494Thiazole-5-carboxylic acid

생성물 1

HCID 25307138N-Methoxy-N-methyl-1,3-thiazole-5-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (2.77 mL, 19.9 mmol) was added slowly to a mixture of commercially available thiazole-5-carboxylic acid (1.03 g, 7.98 mmol), N,O-dimethylhydroxylamine hydrochloride (0.778 g, 7.98 mmol), and EDCI (1.83 g, 9.57 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 72 hours then quenched with saturated aqueous NaHCO3. Water (50 mL) was added followed by additional CH2Cl2. The mixture as stirred for 10 minutes and layers were separated. The CH2Cl2 layer was dried over Na2SO4, then filtered. The solvent was removed under reduced pressure and the residual oil chromatographed (CH2Cl2/EtOAc) to provide the title compound as a white solid.

후처리

  1. customthen quenched with saturated aqueous NaHCO3
  2. additionWater (50 mL) was added
  3. stirringThe mixture as stirred for 10 minutes
  4. customlayers were separated
  5. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residual oil chromatographed (CH2Cl2/EtOAc)

출처 및 근거

ORD 기록
ord-de14795b9123410b8e52f0cf96fc86ae
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290476B2

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